Polymer containing triazole structure, preparation method thereof and light-emitting device
By using crosslinked polymers containing triazole structures as functional layer materials in light emitting diode devices, the problem that functional layer materials are easily dissolved by solvents during solution processing is solved, and the effect of improving the device's thermal stability and solvent resistance is achieved.
Patent Information
- Application Number
- CN202110755542.X
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2021-07-05
- Publication Date
- 2025-05-23
- Estimated Expiration
- 2041-07-05
AI Technical Summary
In the prior art, when preparing light emitting diode devices in solution processing, the functional layer materials are easily dissolved or mutually condensed by the solvent of the next functional layer, resulting in a degradation of device performance.
A polymer containing a triazole structure is used as the material for the electron transport layer and the light emitting layer, and the solvent resistance and thermal stability of the material are improved by crosslinking structural units.
The thermal stability and solvent resistance of the light emitting device film layer are improved, and the film layer is avoided from being affected by the next film layer, thereby improving the overall performance of the light emitting device.
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Figure CN115636923B_ABST
Abstract
Description
Technical Field
[0001] The present application relates to the field of display technology, and in particular to a polymer containing a triazole structure, a preparation method thereof, and a light-emitting device. Background Art
[0002] Solution processing is widely used because it is inexpensive to prepare light-emitting diode devices and can prepare large-area light-emitting diode devices. Light-emitting diode devices are composed of a carrier injection layer, a carrier transport layer, and a light-emitting layer stacked together. If the functional layer of a light-emitting diode device is prepared using the traditional solution processing method, the functional layer material is easily dissolved or miscible with the solvent of the next functional layer during the solution processing process, thereby reducing the performance of the device. Summary of the invention
[0003] The embodiments of the present application provide a polymer containing a triazole structure, a preparation method thereof, and a light-emitting device, so as to improve the thermal stability and solvent resistance of a film layer of the light-emitting device.
[0004] The present application provides a polymer containing a triazole structure, the structural formula of the polymer containing a triazole structure is Among them, the X 1 The structural formula of the group is selected from The X 2 The structural formula of the group is The X 3 The structural formula of the group is The ratio of n to m is 1:(1-99), and the R 1 Group, the R 2 Group, the R 3 Group, the R 4 The group and the R 5 The group is selected from -C 2y H 2y+1 The R 6 The group is C 2x H 2x+1 , y is 1-25, x is 1-25.
[0005] The present application also provides a method for preparing a polymer containing a triazole structure, comprising:
[0006] Providing a first reactant, a second reactant, and a third reactant, wherein the first reactant, the second reactant, and the third reactant react to generate a first intermediate product;
[0007] The first intermediate product is subjected to a first heat treatment to form a polymer containing a triazole structure, wherein the first reactant is a 1The compound of the group, the X 1 The structural formula of the group is selected from The X 2 The structural formula of the group is The X 3 The structural formula of the group is The structural formula of the first intermediate product is The structural formula of the polymer containing triazole structure is The ratio of n to m is 1:(1-99), and the R 1 Group, the R 2 Group, the R 3 Group, the R 4 The group and the R 5 The group is selected from -C 2y H 2y+1 and The R 6 The group is C 2x H 2x+1 , y is 1-25, x is 1-25.
[0008] The present application also provides a light-emitting device, comprising:
[0009] substrate layer;
[0010] an electron transport layer, the electron transport layer being disposed on the substrate layer; and
[0011] A light-emitting layer, wherein the light-emitting layer is disposed on the electron transport layer, wherein the material of the electron transport layer and / or the material of the light-emitting layer comprises a polymer containing a triazole structure, and the structural formula of the polymer containing a triazole structure is Among them, the X 1 The structural formula of the group is selected from The X 2 The structural formula of the group is The X 3 The structural formula of the group is The ratio of n to m is 1:(1-99), and the R 1 Group, the R 2 Group, the R 3 Group, the R 4 The group and the R 5 The groups are independently selected from -C 2y H 2y+1 and The R 6 The group is C 2x H 2x+1 , y is 1-25, x is 1-25.
[0012] The present application provides a polymer containing a triazole structure, a preparation method thereof, and a light-emitting device. The polymer containing a triazole structure is a cross-linked polymer containing a triazole structure. The polymer containing a triazole structure has good solvent resistance and thermal stability. The polymer containing a triazole structure is applied to a light-emitting device, so that a film layer in the light-emitting device has good thermal stability and solvent resistance, and the film layer is prevented from being affected by the next film layer when the light-emitting device is prepared by solution processing, thereby improving the performance of the light-emitting device. BRIEF DESCRIPTION OF THE DRAWINGS
[0013] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the drawings required for use in the description of the embodiments will be briefly introduced below. Obviously, the drawings described below are only some embodiments of the present application. For those skilled in the art, other drawings can be obtained based on these drawings without creative work.
[0014] Figure 1 It is a schematic diagram of the structure of the light-emitting device provided in an embodiment of the present application. DETAILED DESCRIPTION
[0015] The following will be combined with the drawings in the embodiments of the present application to clearly and completely describe the technical solutions in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, not all of the embodiments. Based on the embodiments in the present application, all other embodiments obtained by those skilled in the art without creative work are within the scope of protection of the present application. In addition, it should be understood that the specific implementation methods described herein are only used to illustrate and explain the present application, and are not used to limit the present application. In the present application, unless otherwise stated, the directional words such as "upper" and "lower" used generally refer to the upper and lower parts of the device in actual use or working state, specifically the drawing direction in the accompanying drawings; while "inside" and "outside" refer to the outline of the device.
[0016] The present application provides a polymer containing a triazole structure, a preparation method thereof, and a light-emitting device, which are described in detail below.
[0017] The present application provides a polymer containing a triazole structure, the structural formula of the polymer containing a triazole structure is X 1 The structural formula of the group is selected from X 2 The structural formula of the group is X 3 The structural formula of the group is The ratio of n to m is 1:(1-99), R 1 Group, R 2 Group, R 3 Group, R4 Group and R 5 The groups are independently selected from -C 2y H 2y+1 and R 6 The group is C 2x H 2x+1 , y is 1-25, x is 1-25.
[0018] It should be noted that n and m do not represent the number of specific units of the polymer containing a triazole structure, that is, they do not represent the degree of polymerization, but reflect the molar amount of the two units.
[0019] contain Compounds of the group include
[0020]
[0021]
[0022]
[0023]
[0024] One or a combination of .
[0025] In one embodiment, the structural formula of the polymer containing a triazole structure can be
[0026]
[0027]
[0028]
[0029] wait.
[0030] The present application provides a polymer containing a triazole structure, and the polymer containing a triazole structure is a cross-linkable polymer containing a triazole structure. The polymer containing a triazole structure is composed of a main chain structural unit, an electron transport type structural unit and a cross-linkable structural unit. The main chain structural unit contains a fluorene structural unit or a phenyl-containing side chain structural unit, which has good stability. The electron transport type structural unit contains a triazole structural unit, and the structural unit has good electron transport performance and good heat resistance stability. The cross-linkable structural unit contains a triazole structure and a benzocyclobutene structure, so that the introduction of the cross-linking structural unit will not reduce the electron transport capacity of the film material, and at the same time, the cross-linkable structural unit can be open-loop cross-linked at high temperature to form a film layer insoluble in conventional solvents, so that the polymer containing the triazole structure has good solvent resistance. The triazole-containing polymer constructed of three structural units, namely, the main chain structural unit, the electron transport structural unit and the cross-linkable structural unit, has good thermal stability at room temperature while maintaining the good electron transport performance of the triazole structural unit. In addition, because cross-linking can be achieved at high temperature without producing any by-products, the triazole-containing polymer can be used in light-emitting devices processed by solution technology.
[0031] The present application also provides a method for preparing a polymer containing a triazole structure. The method for preparing a polymer containing a triazole structure comprises:
[0032] A. Provide a first reactant, a second reactant and a third reactant, and the first reactant, the second reactant and the third reactant react to generate a first intermediate product. The first reactant includes X 1 Compounds of the group, X 1 The structural formula of the group is selected from The X 2 The structural formula of the group is The X 3 The structural formula of the group is, and the structural formula of the first intermediate product is The ratio of n to m is 1:(1-99), R 1 Group, R 2 Group, R 3 Group, R 4 Group and R 5 The group is selected from -C 2y H 2y+1 and R 6 The group is C 2x H 2x+1 , y is 1-25, x is 1-25.
[0033] In one embodiment, when the first reactant, the second reactant and the third reactant react to generate a first intermediate product, the corresponding relationship between the molar amount of the first reactant, the molar amount of the first reactant and the molar amount of the third reactant is 4 mmol-7 mmol of the first reactant corresponds to 0.1 mmol-2 mmol of the second reactant and 2 mmol-5 mmol of the third reactant.
[0034] In one embodiment, the first reactant, the second reactant and the third reactant react in a solvent to generate a first intermediate product, and the solvent includes one or a combination of toluene, ethanol, ethylene, perchloroethylene, trichloroethylene, acetone, ethylene glycol ether and triethanolamine.
[0035] The step of reacting the first reactant, the second reactant and the third reactant to generate the first intermediate product comprises:
[0036] performing a second heat treatment on the first reactant, the second reactant and the third reactant to generate a second intermediate product;
[0037] The second intermediate product is subjected to a third heat treatment to generate a first intermediate product.
[0038] In one embodiment, the temperature of the second heat treatment is 100 degrees Celsius to 120 degrees Celsius.
[0039] In one embodiment, the second heat treatment lasts for 5 hours to 24 hours.
[0040] In one embodiment, the temperature of the third heat treatment is 85 degrees Celsius to 110 degrees Celsius.
[0041] In one embodiment, the structural formula of the first reactant can be The structural formula of the second reactant can be The structural formula of the third reactant can be
[0042] In one embodiment, the reaction formula for generating the first intermediate product by reacting the first reactant, the second reactant and the third reactant may be:
[0043]
[0044] In one embodiment, 5.3 mmol of fluorene borate derivative is added to a 100 ml two-necked bottle. 4.4 mmol 0.8 mmol of benzocyclobutene derivative Then, add 27.04 micromoles of tri(2-methoxyphenyl)phosphine as a catalyst ligand; then, add 5.1 micromoles of palladium acetate Pd(OAc)2 as a catalyst; then, perform a vacuum and nitrogen exchange operation, repeat 3 times; then, add 20wt% tetraethylammonium hydroxide solution with a syringe; then, add 60 ml of toluene, reflux at 110 degrees Celsius for 6 hours under a nitrogen atmosphere; then, add 3.2 millimoles of phenylboric acid to the mixed solution, and continue to react for 12 hours; after the reaction is completed, add sodium diethyldithiocarbamate solution to the mixed solution, and stir at 85 degrees Celsius for 2 hours; then, wash the oil phase with water several times, and separate and purify it with a chromatographic column; after purification, use methanol to precipitate it, filter it, and dry it. The first intermediate product is obtained. The molecular weight is determined by high-performance gel chromatography, and its Mn=69000 and Mw=160000 are measured.
[0045] In the present application, the addition of phenylboronic acid can be used to terminate the active bromine end group, thereby improving the stability of the first intermediate product and avoiding luminescence quenching.
[0046] In one embodiment, the structural formula of the first reactant can be The structural formula of the second reactant can be The structural formula of the third reactant can be
[0047] In one embodiment, the reaction formula for generating the first intermediate product by reacting the first reactant, the second reactant and the third reactant may be:
[0048]
[0049] In one embodiment, 4.5 mmol of fluorene borate derivative was added to a 100 ml two-necked flask. 3 mmol 1 mmol of benzocyclobutene derivative Then, add 27.04 micromoles of tri(2-methoxyphenyl)phosphine as a catalyst ligand; then, add 5.1 micromoles of palladium acetate Pd(OAc)2 as a catalyst; then, vacuumize and replace nitrogen, repeat 3 times; then, add 20wt% tetraethylammonium hydroxide solution with a syringe; then, add 60 ml of toluene, reflux at 115 degrees Celsius for 8 hours under a nitrogen atmosphere; then, add 3.2 millimoles of phenylboric acid to the mixed solution, and continue to react for 20 hours; after the reaction is completed, add sodium diethyldithiocarbamate solution to the mixed solution, and stir at 90 degrees Celsius for 3 hours; then, wash the oil phase with water several times, and separate and purify it with a chromatographic column; after purification, precipitate it with methanol, filter it, and dry it. The first intermediate product is obtained. The molecular weight is determined by high-performance gel chromatography, and its Mn=72000 and Mw=159000 are measured.
[0050] In one embodiment, the structural formula of the first reactant can be The structural formula of the second reactant can be The structural formula of the third reactant can be
[0051] In one embodiment, the reaction formula for generating the first intermediate product by reacting the first reactant, the second reactant and the third reactant may be:
[0052]
[0053] In one embodiment, 6 mmol of fluorene borate derivative is added to a 100 ml two-necked flask in sequence: 2.5 mmol 1.6 mmol of benzocyclobutene derivative Then, add 27.04 micromoles of tri(2-methoxyphenyl)phosphine as a catalyst ligand; then, add 5.1 micromoles of palladium acetate Pd(OAc)2 as a catalyst; then, vacuumize and replace nitrogen, repeat 3 times; then, add 20wt% tetraethylammonium hydroxide solution with a syringe; then, add 60 ml of toluene, reflux at 105 degrees Celsius for 8 hours under a nitrogen atmosphere; then, add 3.2 millimoles of phenylboric acid to the mixed solution, and continue to react for 15 hours; after the reaction is completed, add sodium diethyldithiocarbamate solution to the mixed solution, and stir at 95 degrees Celsius for 1.5 hours; then, wash the oil phase with water several times, and separate and purify it with a chromatographic column; after purification, precipitate it with methanol, filter it, and dry it. The first intermediate product is obtained. The molecular weight is determined by high-performance gel chromatography, and its Mn=75000 and Mw=170000 are measured.
[0054] In one embodiment, the second reactant is formed by a fourth reactant and a fifth reactant. The fourth reactant has a structural formula of The structural formula of the fifth reactant is
[0055] In one embodiment, the reaction formula for the fourth reactant and the fifth reactant to generate the second reactant may be:
[0056]
[0057] In one embodiment, 30 mmol of Then 10 mmol of POCl 3 After the reaction is complete, return to room temperature and add 5 mmol of Then, nitrogen was passed through the flask to make it in a nitrogen atmosphere, and the reaction liquid was heated to reflux for 8 hours; then, the reaction liquid was cooled to room temperature. After the reaction was completed, the reaction liquid was filtered; then, extraction and separation were performed, and then the reaction liquid was separated and purified by silica gel chromatography, using n-hexane / ethyl acetate as eluent, and the solvent was removed by rotary evaporation to collect the product, and finally vacuum dried at room temperature for 12 hours to obtain the second reactant, which was weighed and had a yield of about 61%.
[0058] 1HNMR (300MHz, DMSO), (TMS, ppm): 7.68 (s, 2H), 7.66-7.62 (m, 8H), 7.20 (d, 1H), 7.07 (d, 1H), 2.88 (s, 4H).
[0059] In one embodiment, the third reactant is formed by the fourth reactant and the sixth reactant. The structural formula of the fourth reactant is The structural formula of the sixth reactant is
[0060] In one embodiment, the reaction formula for the fourth reactant and the sixth reactant to generate the third reactant may be:
[0061]
[0062] In one embodiment, 30 mmol of Then 10 mmol of POCl 3 After the reaction is complete, return to room temperature and add 5 mmol of Then, nitrogen was passed through the flask to make it in a nitrogen atmosphere, and the reaction liquid was heated to reflux for 8 hours; then, the reaction liquid was cooled to room temperature. After the reaction was completed, the reaction liquid was filtered, and then extracted and separated. Then, the reaction liquid was separated and purified by a silica gel column, and n-hexane / ethyl acetate was used as an eluent. The solvent was removed by rotary evaporation to collect the product, and finally vacuum dried at room temperature for 12 hours to obtain the third reactant, which was weighed and had a yield of about 60%.
[0063] 1HNMR (300MHz, DMSO), (TMS, ppm):
[0064] 7.66-7.62(m, 8H), 7.32(d, 1H), 7.17(d, 2H), 2.55(m, 1H), 1.52(m, 2H), 1.16(m, 3H), 0.76(m, 3H).
[0065] B. performing a first heat treatment on the first intermediate product to form a polymer containing a triazole structure, wherein the polymer containing a triazole structure has a structural formula of
[0066] In one embodiment, the temperature of the first heat treatment is 110 degrees Celsius to 250 degrees Celsius.
[0067] In one embodiment, the general reaction formula for performing a first heat treatment on the first intermediate product to form a polymer containing a triazole structure may be:
[0068]
[0069] In one embodiment, the structural formula of the first intermediate product can be
[0070] In one embodiment, the reaction formula for the first intermediate product to react to generate a polymer containing a triazole structure may be:
[0071]
[0072] The first intermediate product is baked at 120 degrees Celsius for 10 minutes to remove the residual solvent; then, it is subjected to a first heat treatment to form a polymer containing a triazole structure.
[0073] The temperature of the first heat treatment is 110 degrees Celsius to 250 degrees Celsius. Specifically, the temperature of the first heat treatment may be 110 degrees Celsius, 150 degrees Celsius, 200 degrees Celsius, 220 degrees Celsius or 250 degrees Celsius, etc. In this embodiment, the temperature of the first heat treatment is 200 degrees Celsius.
[0074] The first heat treatment time is 30 minutes to 60 minutes. Specifically, the first heat treatment time can be 30 minutes, 33 minutes, 40 minutes, 50 minutes or 60 minutes.
[0075] It should be noted that n and m do not represent the number of specific units of the polymer containing a triazole structure, that is, they do not represent the degree of polymerization, but reflect the molar amount of the two units.
[0076] In the present application, since the proportion of n in the entire main chain can mainly control the proportion of cross-linkable structural units and the solubility of the polymer containing the triazole structure, the ratio of n to m is set to 1: (1-99), which can improve the cross-linking and stability of the first intermediate product. If the proportion of cross-linkable structural units is too high, it is easy to cause incomplete reaction of some cross-linkable structural units, thereby leading to quenching of luminescence and increased instability of the first intermediate product.
[0077] The present application provides a method for preparing a polymer containing a triazole structure. The polymer containing a triazole structure is a cross-linked polymer containing a triazole structure. The polymer containing a triazole structure is applied to a light-emitting device, so that the film layer in the light-emitting device has good thermal stability and solvent resistance, and the film layer is prevented from being affected by the next film layer when the light-emitting device is prepared by solution processing, thereby improving the performance of the light-emitting device.
[0078] See also Figure 1 , Figure 1 1 is a schematic diagram of the structure of a light emitting device provided in an embodiment of the present application. The present application also provides a light emitting device. The light emitting device 10 includes a substrate layer 100, an electron transport layer 200 and a light emitting layer 300. The specific description is as follows.
[0079] In one embodiment, the light emitting device 10 further includes a cathode 400. The cathode 400 is disposed on the substrate layer 100.
[0080] In one embodiment, the material of the cathode 400 includes one or a combination of indium tin oxide, indium zinc oxide, aluminum zinc oxide, and indium gallium zinc oxide. In this embodiment, the material of the cathode 400 is indium tin oxide.
[0081] In one embodiment, the light emitting device 10 further includes an electron injection layer 500 . The electron injection layer 500 is disposed on the cathode 400 .
[0082] The electron transport layer 200 is disposed on the electron injection layer 500 .
[0083] The light emitting layer 300 is disposed on the electron transport layer 200 .
[0084] In one embodiment, the material of the electron transport layer 200 includes the above-mentioned polymer containing a triazole structure.
[0085] In the present application, a polymer containing a triazole structure is used to prepare the electron transport layer 200, so that the electron transport layer 200 can improve its thermal stability and solvent resistance while ensuring its own performance. When the light-emitting device 10 is prepared by a solution processing process, the electron transport layer 200 can be prevented from being affected by the next film layer, thereby improving the performance of the light-emitting device 10.
[0086] In one embodiment, the material of the electron transport layer 200 does not contain the aforementioned polymer containing a triazole structure, but the material of the light emitting layer 300 contains the aforementioned polymer containing a triazole structure.
[0087] In the present application, a polymer containing a triazole structure is used to prepare the light-emitting layer 300, so that the light-emitting layer 300 can improve its thermal stability and solvent resistance while ensuring its own performance. When the light-emitting device 10 is prepared by a solution processing technology, the light-emitting layer 300 can be prevented from being affected by the next film layer on the light-emitting layer 300, that is, the light-emitting layer 300 is prevented from being dissolved by the solvent of the next film layer, thereby improving the performance of the light-emitting device 10.
[0088] In one embodiment, the material of the light emitting layer 300 and the material of the electron transport layer 200 both contain the aforementioned polymer containing a triazole structure.
[0089] In the present application, a polymer containing a triazole structure is used to prepare the light-emitting layer 300 and the electron transport layer 200, so that the light-emitting layer 300 and the electron transport layer 200 can improve their thermal stability and solvent resistance while ensuring their own performance. When the light-emitting device 10 is prepared by a solution processing process, the light-emitting layer 300 and the electron transport layer 200 can be prevented from being affected by the next film layer on the light-emitting layer, that is, the light-emitting layer 300 and the electron transport layer 200 are prevented from being dissolved by the solvent of the next film layer, thereby improving the performance of the light-emitting device 10.
[0090] In one embodiment, the light emitting device 10 further includes a hole transport layer 600, a hole injection layer 700 and an anode 800. The hole transport layer 600, the hole injection layer 700 and the anode 800 are sequentially stacked on the light emitting layer 300.
[0091] The present application provides a light-emitting device 10, which includes a substrate layer 100, and an electron transport layer 200 and a light-emitting layer 300 sequentially stacked on the substrate layer 100. The material of the electron transport layer 200 and / or the material of the light-emitting layer 300 is a polymer containing a triazole structure as described in the present application, so that the electron transport layer 200 and / or the light-emitting layer 300 can improve the thermal stability and solvent resistance of the electron transport layer 200 and / or the light-emitting layer 300 while ensuring its own performance, thereby improving the performance of the light-emitting device 10.
[0092] The present application also provides a method for preparing a light emitting device. The method for preparing the light emitting device 10 of the present application is described by taking the example of forming an electron transport layer 200 with a polymer containing a triazole structure. The specific description is as follows.
[0093] Example
[0094] A substrate layer 100 is provided. Then, a cathode 400 is formed on the substrate layer 100.
[0095] Then, the substrate layer 100 and the cathode 400 are cleaned in the following order: 5% potassium hydroxide solution ultrasonic for 15 minutes, pure water ultrasonic for 15 minutes, isopropanol ultrasonic for 15 minutes, and oven drying for 1 hour. Then, the substrate layer 100 and the cathode 400 are transferred to the ultraviolet ozone cleaning equipment for surface treatment for 15 minutes. After the treatment, they are immediately transferred to the glove box. A layer of zinc oxide nanoparticles is spin-coated on the clean cathode 400. Then, it is baked at a temperature of 120 degrees Celsius for 15 minutes.
[0096] Then, after dissolving the first intermediate product with a solvent (such as o-xylene), the first intermediate product is spin-coated on the zinc oxide nanolayer, and the first intermediate product is first baked at 120 degrees Celsius for 10 minutes to remove the residual solvent. Then, the first intermediate product is ring-opened and cross-linked at 200 degrees Celsius to form a polymer containing a triazole structure, that is, to form an electron transport layer 200. The cross-linking time is 30 minutes to 60 minutes.
[0097] The structural formula of the first intermediate product may be (Formula 1)-(Formula 16). In this embodiment, the electron transport layer is prepared using Formula 1-Formula 16 respectively.
[0098] Then, the ink of the light-emitting layer 300 is spin-coated. Then, the hole transport layer 600, the hole injection layer 700 and the anode 800 are formed by vacuum evaporation. Finally, the package is cured by ultraviolet light and heated and baked for 20 minutes to prepare the light-emitting device 10.
[0099] Comparative Example
[0100] A substrate layer is provided and then an anode is formed on the substrate layer.
[0101] Then, the substrate layer and the anode were cleaned in the following order: 5% potassium hydroxide solution ultrasonic for 15 minutes, pure water ultrasonic for 15 minutes, isopropanol ultrasonic for 15 minutes, and oven drying for 1 hour. Then, the substrate layer and the anode were transferred to the UV ozone cleaning equipment for surface treatment for 15 minutes. After treatment, they were immediately transferred to the glove box. A layer of zinc oxide nanoparticles was spin-coated on the clean anode. Then, it was baked at a temperature of 120 degrees Celsius for 15 minutes.
[0102] Then, the electron transport layer material is deposited by vacuum evaporation. The electron transport layer material is TPBi. The evaporation rate is 0.1 nm / s.
[0103] Then, after spin coating the light-emitting layer ink, vacuum evaporation was used to form a hole transport layer, a hole injection layer and a cathode. Finally, the package was cured by ultraviolet light and heated and baked for 20 minutes to prepare a light-emitting device.
[0104] Please refer to Table 1, which shows data of light-emitting devices using a polymer containing a triazole structure to form an electron transport layer and / or a light-emitting layer.
[0105] Table 1
[0106]
[0107]
[0108] The structure of device 1-16 is Al / ZnO (35nm) / Formula 1-Formula 16 (20nm) / mCP:Ir(ppy)2acac, 7wt% (30nm) / TAPC (30nm) / NPB (10nm) / HAT-CN (10nm) / ITO (120nm), wherein Al is the cathode material. ZnO is the electron injection layer material. Formula 1-Formula 16 are the electron transport layer materials. mCP is the main material of the light-emitting layer, and Ir(ppy)2acac is the guest material of the light-emitting layer. TAPC and NPB are hole transport layer materials. HAT-CN is the hole injection layer material. ITO is the anode material.
[0109] The structure of the light-emitting device in the comparative example is Al / ZnO (35nm) / TPBi (20nm) / mCP:Ir(ppy)2acac, 7wt% (30nm) / TAPC (30nm) / NPB (10nm) / HAT-CN (10nm) / ITO (120nm), wherein Al is the cathode material. ZnO is the electron injection layer material. TPBi is the electron transport layer material. mCP is the main material of the light-emitting layer, and Ir(ppy)2acac is the guest material of the light-emitting layer. TAPC and NPB are hole transport layer materials. HAT-CN is the hole injection layer material. ITO is the anode material.
[0110] It should be noted that CIEx and CIEy are the values of color coordinates. As can be seen from Table 1, the use of the first intermediate product to form a polymer containing a triazole structure, that is, to form an electron transport layer 200, makes the electron transport layer 200 have good thermal stability and solvent resistance, while not affecting the current efficiency and luminescence performance of the light-emitting device 10, thereby improving the performance of the light-emitting device 10.
[0111] The present application provides a method for preparing a light-emitting device, in which a polymer containing a triazole structure is used to form an electron transport layer. Since the polymer containing a triazole structure has high thermal stability and solvent resistance, it is used in the electron transport layer 200, so that the electron transport layer 200 has good thermal stability and solvent resistance while ensuring its own performance, thereby improving the performance of the light-emitting device 10.
[0112] The present application provides a polymer containing a triazole structure, a preparation method thereof, and a light-emitting device. The polymer containing a triazole structure is a cross-linked polymer containing a triazole structure. The polymer containing a triazole structure is applied to a light-emitting device, so that the film layer in the light-emitting device has good thermal stability and solvent resistance, and the film layer is prevented from being affected by the next film layer when the light-emitting device is prepared by solution processing, thereby improving the performance of the light-emitting device.
[0113] The above is a detailed introduction to a polymer containing a triazole structure, a preparation method thereof, and a light-emitting device provided in the embodiments of the present application. Specific examples are used herein to illustrate the principles and implementation methods of the present application. The description of the above embodiments is only used to help understand the method of the present application and its core idea. At the same time, for technicians in this field, according to the ideas of the present application, there will be changes in the specific implementation methods and application scopes. In summary, the content of this specification should not be understood as a limitation on the present application.
Claims
1. A polymer containing a triazole structure, It is characterized in that The structural formula of the polymer containing triazole structure is Among them, the X 1 The structural formula of the group is selected from The X 3 The structural formula of the group is The ratio of n to m is 1:(1-99), and the R 1 Group, the R 2 Group, the R 3 Group, the R 4 The group and the R 5 The groups are independently selected from -C 2y H 2y+1 or The R 6 The group is C 2x H 2x+1 , y is 1-25, x is 1-25.
2. The polymer containing a triazole structure according to claim 1, It is characterized in that The polymer is formed by ring-opening and cross-linking of a first intermediate product through a first heat treatment, wherein the first intermediate product comprises: One or a combination of the following.
3. The polymer containing a triazole structure according to claim 1, It is characterized in that The structural formula of the polymer containing triazole structure includes One or several combinations thereof.
4. A method for preparing a polymer containing a triazole structure, It is characterized in that include: Providing a first reactant, a second reactant, and a third reactant, wherein the first reactant, the second reactant, and the third reactant react to generate a first intermediate product; The first intermediate product is subjected to a first heat treatment to form a polymer containing a triazole structure, wherein the first reactant is a 1 The compound of the group, the X 1 The structural formulas of the groups are independently selected from The second reactant is selected from The third reactant comprises X 3 The compound of the group, the X 3 The structural formula of the group is The structural formula of the polymer containing triazole structure is The ratio of n to m is 1:(1-99), and the R 1 Group, the R 2 Group, the R 3 Group, the R 4 The group and the R 5 The groups are independently selected from -C 2y H 2y+1 or The R 6 The group is C 2x H 2x+1 , y is 1-25, x is 1-25.
5. The method for preparing the polymer containing triazole structure according to claim 4, It is characterized in that In the reaction among the first reactant, the second reactant and the third reactant to generate a first intermediate product, the corresponding relationship among the molar amount of the first reactant, the molar amount of the first reactant and the molar amount of the third reactant is 4 mmol-7 mmol of the first reactant corresponds to 0.1 mmol-2 mmol of the second reactant and 2 mmol-5 mmol of the third reactant.
6. The method for preparing the polymer containing triazole structure according to claim 4, It is characterized in that The temperature of the first heat treatment is 110 degrees Celsius to 250 degrees Celsius.
7. The method for preparing the polymer containing triazole structure according to claim 4, It is characterized in that The first reactant, the second reactant and the third reactant react in a solvent to generate a first intermediate product, and the solvent includes one or a combination of toluene, ethanol, ethylene, perchloroethylene, trichloroethylene, acetone, ethylene glycol ether and triethanolamine.
8. A light emitting device, It is characterized in that include: substrate layer; An electron transport layer, wherein the electron transport layer is disposed on the substrate layer; as well as A light-emitting layer, wherein the light-emitting layer is disposed on the electron transport layer, wherein the material of the electron transport layer and / or the material of the light-emitting layer comprises a polymer containing a triazole structure, and the structural formula of the polymer containing a triazole structure is Among them, the X 1 The structural formula of the group is selected from The X 3 The structural formula of the group is The ratio of n to m is 1:(1-99), and the R 1 Group, the R 2 Group, the R 3 Group, the R 4 The group and the R 5 The groups are independently selected from -C 2y H 2y+1 or The R 6 The group is C 2x H 2x+1 , y is 1-25, x is 1-25.
9. The light emitting device according to claim 8, It is characterized in that The polymer is formed by ring-opening and cross-linking of a first intermediate product through a first heat treatment, wherein the first intermediate product comprises: One or a combination of the following.
10. The light emitting device according to claim 8, It is characterized in that The structural formula of the polymer containing triazole structure includes One or a combination of .
Citation Information
Patent Citations
Light emitting device
JP2017108134A
compound
US20200321532A1